CN109689723A - Glycol composition - Google Patents

Glycol composition Download PDF

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Publication number
CN109689723A
CN109689723A CN201780055221.0A CN201780055221A CN109689723A CN 109689723 A CN109689723 A CN 109689723A CN 201780055221 A CN201780055221 A CN 201780055221A CN 109689723 A CN109689723 A CN 109689723A
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China
Prior art keywords
glycol composition
polyol
cell foam
rigid closed
glycol
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Granted
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CN201780055221.0A
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Chinese (zh)
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CN109689723B (en
Inventor
R·里乔
I·阿米奇-克若提拉瓦
G·瓦罗
P·库克森
F·M·卡萨蒂
E·费拉里
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Dow Global Technologies LLC
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Dow Global Technologies LLC
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    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
    • C08G18/0876—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic the dispersing or dispersed phase being a polyol
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    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
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    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
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    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
    • C08G18/4219—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from aromatic dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
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    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
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Abstract

Embodiment of the disclosure is related to glycol composition, it includes the dispersion of the polyisocyanate polyaddition particle in carrier polyol, wherein the average grain diameter of the polyisocyanate polyaddition particle is 0.1 to 10.0 microns, and with the total weight of the dispersion, the solid content of the dispersion is 5wt% to 50wt%, with with the total weight of the glycol composition, the polyester polyol of 1wt% to the 98wt% of the glycol composition.

Description

Glycol composition
Technical field
Embodiment of the disclosure is related to glycol composition, and more specifically, embodiment, which is related to can be used to form hard, closes The glycol composition of the foam in hole.
Background technique
Foam is that wherein gas is dispersed in the dispersion in fluent material, solid material or gel rubber material.It can be by polynary The chemical reaction of pure and mild isocyanates forms foam.Foam can be used for multiple and different applications, including bedding, furniture, vehicle Seat, heat insulator and carpet backing etc..
Summary of the invention
The disclosure provides glycol composition comprising the dispersion of the polyisocyanate polyaddition particle in carrier polyol Body, wherein the average grain diameter of polyisocyanate polyaddition particle is 0.1 to 10.0 microns, and with the total weight of dispersion, is divided The solid content of granular media is 5wt% to 50wt%, and with the total weight of glycol composition, the 1wt% of glycol composition To the polyester polyol of 98wt%.
It includes glycol composition that the disclosure, which provides,；Foaming agent；With the rigid closed-cell foam formulation of polyisocyanates.
The disclosure provides the rigid closed-cell foam formed by rigid foam formulation.
The disclosure provides the method for being used to form rigid closed-cell foam comprising solidification rigid closed-cell foam formulation.
The above summary of the invention of the disclosure is not intended to each embodiment party for describing each disclosed embodiment or the disclosure Case.More specifically illustrative embodiment is described below.In the several places entirely applied, referred to by example list offer It leads, the example various can be applied in combination.In each case, the list described functions only as representative group without that should solve It is interpreted as exclusive list.
Specific embodiment
Glycol composition, rigid closed-cell foam formulation including glycol composition is disclosed herein and is formed by it Rigid closed-cell foam.Polyalcohol (such as glycol composition disclosed herein) can be combined with isocyanates to form rigid closed cell Foam formulation.Rigid closed-cell foam formulation is curable to form rigid closed-cell foam, is referred to alternatively as polyurethane or gathers different Cyanurate.
Polyurethane be include polymer by the chain for the unit for being referred to alternatively as the carbamate key connecting of ammonia ester bond. PIR (poly-isocyanurate) has the isocyanuric acid ester of high-content.
As mentioned, rigid closed-cell foam formulation disclosed herein can be used to form rigid closed-cell foam.These hard Closed-cell foam can have the various desired characteristics of application.For example, disclosed herein hard compared with other rigid closed-cell foams Matter closed-cell foam can have improvement (that is, reduction) mean cell diameter.This reduce mean cell diameter be it is unexpected, Because of the polyisocyanate cyanogen in carrier polyol that rigid closed-cell foam disclosed herein is 5wt% to 50wt% using solid content The dispersion of acid esters addition polymerization (PIPA) particle.It has been observed that for example such as being discussed in WO 99/60045, styrene and/or styrene The aperture of acrylonitrile polymers polyalcohol (it includes solids) generation high-content.Aperture a part of obvious high-content by In the solid content of styrene and/or styrene-acrylonitrile copolymer nitrile polymer polyalcohol, serves as abscess and disintegrate agent.
In addition, rigid closed-cell foam disclosed herein can have improvement (that is, reducing compared with other rigid closed-cell foams ) thermal conductivity.Although without being bound by theory, it is believed that compared with other rigid closed-cell foams, reduced rigid closed cell bubble The mean cell diameter of foam can help to provide reduced thermal conductivity.
In addition, rigid closed-cell foam formulation disclosed herein can have the various desired multiple curing characteristics of application.It lifts For example, compared with the curing properties of other foam formulations, rigid closed-cell foam formulation disclosed herein can have can phase When cream time, gel time and/or tack-free times.
Glycol composition is disclosed herein.As used herein, " polyalcohol " refers to that each molecule has and is averagely greater than 1.0 The organic molecule of hydroxyl, such as polyester.
Glycol composition disclosed herein includes the dispersion of the PIPA particle in carrier polyol and with polyalcohol The total weight of composition, the polyester polyol of 1wt% to the 98wt% of glycol composition.Dispersion includes carrier polyol And solids, i.e., PIPA particle dispersed therein.
The dispersion of the particle of PIPA can be formed by a variety of methods in carrier polyol；Such methods are in WO2015/ It is discussed in 038825 and WO2015/038826, it is therein to be each incorporated herein by reference.As an example, The dispersion of PIPA particle in carrier polyol can be used as the equivalent weight of the quantity averagely hydrogen compound containing isocyanate-reactive Measuring the hydrogen compound containing isocyanate-reactive of the low equivalent less than 80 and being dispersed in quantity average hydroxyl equivalent is 200 to 2000 Quantity isocyanide in the carrier polyol of (wherein in terms of the total amount of the hydroxyl in carrier polyol at least 50% is secondary hydroxyl) The reaction product of polyisocyanates of the acid esters equivalent less than 225 is formed.Reaction can execute in situ, such as contain isocyanide in low equivalent When acid esters reactive hydrogen compound and polyisocyanates reactant are dispersed or dissolved in carrier polyol, wherein in low equivalent Hydroxyl in hydrogen compound containing isocyanate-reactive and carrier polyol is reacted with the isocyanate group in polyisocyanates. Reaction between the pure and mild polyisocyanates of carrier polyol can produce grafting.Grafting can help to stablize in carrier polyol The dispersion of PIPA particle.However, excess or grafting have contained little or no dispersin polymerization there may be high viscosity product Object phase.Therefore, when the dispersion for the PIPA particle being formed in carrier polyol, such as polyurethane or polyurethane-urea are formed The reaction of key can be balanced with graft reaction.This balance can be bigger more reactive than carrier polyol to isocyanate group by selection The hydrogen compound containing isocyanate-reactive of low equivalent provides the grafting of sufficient amount still simultaneously to form stabilising dispersions, and It is realized optionally by such as catalyst choice and the catalyst concn in reactant and/or the stabilizer for dispersion.
With the total weight of dispersion, the solid content of the dispersion of the PIPA particle in carrier polyol can be 5wt% to 50wt%.All individual values and subrange including 5wt% to 50wt%；Such as in carrier polyol Total weight (such as summation of the weight of PIPA particle and carrier polyol) meter of the dispersion of PIPA particle, in carrier polyol In PIPA particle dispersion solid content can for be limited under 5wt%, 10wt% or 15wt% 50wt%, 45wt% or The upper limit of 40wt%.In other words, solid content refers to the weight of the PIPA particle of the percentage of the total weight of dispersion.It lifts For example, the weight of PIPA particle can be the calculated weight measured according to method known in fields.
The average grain diameter of PIPA particle can be 0.1 to 10.0 microns.Including 0.1 to 10.0 microns of all individual values and son Range；Such as the average grain diameter of PIPA particle can arrive for 0.1,0.2,0.3,0.4,0.5,0.8,1.0 or 1.5 micron of lower range 10.0,9.0,8.0,7.0,6.0,5.0,4.5,4.0 or 3.5 upper range.One or more other embodiments of the present disclosure are provided to The average grain diameter of the PIPA particle of few 90wt% can be 0.1 to 5.0 microns；Such as 90wt%, 91wt%, 92wt%, 93wt%, The average grain diameter of the PIPA particle of 94wt%, 95wt% or even higher weight % can be 0.1 to 5.0 microns.
The PIPA particle dispersion that one or more other embodiments of the present disclosure are provided in carrier polyol can be used as low work as The hydrogen compound containing isocyanate-reactive of amount and the reaction product of polyisocyanates are formed.The one or more of the disclosure implement The hydrogen compound containing isocyanate-reactive that example provides low equivalent is polyalcohol.One or more other embodiments of the present disclosure provide low The quantity average isocyanate ester reactive hydrogen equivalent weight of the hydrogen compound containing isocyanate-reactive of equivalent is at most 80g/ mol.For example, the quantity average isocyanate ester reactive hydrogen equivalent weight of the hydrogen compound containing isocyanate-reactive of low equivalent Amount can arrive 80g/mol for 50.The hydrogenation containing isocyanate-reactive that one or more other embodiments of the present disclosure provide low equivalent is closed The quantity average isocyanate ester reactive hydrogen equivalent weight of object is less than 80.Quantity average hydroxyl equivalent can be calculated as molecular weight and The quotient of average functionality, that is, molecular weight is divided by average functionality.This average functionality can be calculated as isocyanate-reactive hydrogen Amount to mole and polyalcohol amount to mole quotient.One or more other embodiments of the present disclosure offer low equivalent contains isocyanic acid The each molecule of ester reactive hydrogen compound may include 2 to 6 isocyanate-reactive hydrogen groups, such as hydroxyl and/or amine.This public affairs The each molecule of hydrogen compound containing isocyanate-reactive that the one or more embodiments opened provide low equivalent may include 2 to 6 Amino.
In the dispersion for the PIPA particle being formed in carrier polyol, low equivalent is hydrogenated containing isocyanate-reactive Closing object can be for example dispersed in carrier polyol in the form of droplet.The low equivalent utilized is hydrogenated containing isocyanate-reactive The amount for closing object can be enough to consume the isocyanate group provided in the reactive mixture.For example, for the isocyanic acid of every equivalent The hydroxyl equivalent of the hydrogen compound containing isocyanate-reactive of the low equivalent of ester group, is used to form the PIPA in carrier polyol The polyisocyanates index of the dispersion of particle can be 30 to 200.Including 30 to 200 all individual values and subrange；Such as For the equivalent of the hydroxyl of the hydrogen compound containing isocyanate-reactive of the isocyanate group low equivalent of every equivalent, it is used to form The polyisocyanates index of the dispersion of PIPA particle in carrier polyol can be limited to 200 under 30,40,50 or 60, 175,150,120,110 or 105 upper limit.Polyisocyanates index can be measured as the PIPA being used to form in carrier polyol The equivalent of the isocyanates in the reactive mixture of the dispersion of particle is reacted divided by isocyanates in the reactive mixture The total yield of property hydrogen, multiplied by 100.In other words, isocyanate index is being present in reaction mixture of being given as percentages Isocyanate group and isocyanate reactive hydrogen atoms ratio.
In the dispersion for the PIPA particle being formed in carrier polyol, every 100 parts by weight carrier polyol, low equivalent Hydrogen compound containing isocyanate-reactive can be with 1 parts by weight to the amount of 50 parts by weight, such as 2 parts to 30 parts or 2 parts to 25 parts Deng use.Including 1 part to 50 parts of all individual values and subrange；Such as every 100 parts by weight carrier polyol, low equivalent contain Isocyanate-reactive hydrogen compound can be to be limited to 50,40,30,20,15,10 or 7 parts by weight under 1,2,3 or 4 parts by weight The upper limit uses.
The example of the hydrogen compound containing isocyanate-reactive of low equivalent includes but is not limited to ethylene glycol, diethylene glycol, three Ethylene glycol, 1,3- propylene glycol, 1,2- propylene glycol, dipropylene glycol, tripropylene glycol, glycerine, trimethylolpropane, trihydroxy methyl second Alkane, pentaerythrite, erythritol, sucrose, ethanol amine, such as triethanolamine and diethanol amine and a combination thereof.
As mentioned, the dispersion of the PIPA particle in carrier polyol can be used as reacting containing isocyanates for low equivalent The reaction product of property hydrogen compound and polyisocyanates is formed.One or more other embodiments of the present disclosure provide polyisocyanates Quantity average isocyanate ester equivalent is 50g/mol to 225g/mol.All individual values and subrange for arriving 225g/mol including 50； Such as the quantity average isocyanate ester equivalent of polyisocyanates can be limited to 225 under 50,55,60,65 or 70g/mol, 200, The upper limit of 175 or 150g/mol.Polyisocyanates can be aromatic series, cyclic aliphatic or aliphatic polyisocyante.Polyisocyanates Example include but is not limited to metaphenylene diisocyanate (MDI), toluene di-isocyanate(TDI) (TDI), two isocyanide of hexa-methylene Acid esters (HDI), tetramethylene diisocyanate, cyclohexane diisocyanate, hexahydrotoluene diisocyanate, two isocyanide of naphthylene Acid esters, bis- (isocyanatomethyl) hexamethylenes and a combination thereof.One or more other embodiments of the present disclosure provide polyisocyanates Including TDI and/or MDI, such as by trade (brand) name VORANATE and ISONATE purchased from Dow Chemical (The Dow Chemical Company).As an example, polyisocyanates may include the mixture of the different isomer of TDI or MDI, Such as including 60% to 85% TDI 2,4'- isomers and 15% to 40% TDI 2,6' isomers mixture.
The dispersion of PIPA particle includes carrier polyol.Carrier polyol can be polyethers, polyester, polycarbonate, fourth two Polymer, the acryl polyol of alkene, or combinations thereof etc..For example, carrier polyol may include discussed herein One of polyester polyol or a variety of etc..It is that polyethers is more that one or more other embodiments of the present disclosure, which provide carrier polyol, First alcohol.For example, carrier polyol can be polyether polyol, such as propylene oxide homopolymers or propylene oxide and ethylene oxide Copolymer, " polyethers " refers to the compound comprising two or more ehter bonds connection, such as polyalcohol.Carrier polyol is averaged Molecular weight can be 600 to 12000.Including 600 to 12000 all individual values and subrange；Such as carrier polyol is averaged Molecular weight can be limited to 12000 under 600,700,800,900 or 1000,11000,10000,9000,8000,7000,6000, 5000,4500 or 4000 upper limit.The hydroxyl value of carrier polyol is 25mgKOH/g to 350mg KOH/g.Including 25mg All individual values and subrange of KOH/g to 350mg KOH/g；Such as the hydroxyl value of carrier polyol can be 25,30 or 35mg The upper limit of 350,300,250,200 or 150mg KOH/g is limited under KOH/g.The quantity average hydroxyl equivalent of carrier polyol It can be 200g/mol to 2000g/mol.All individual values and subrange for arriving 2000g/mol including 200；Such as carrier polyol Quantity average hydroxyl equivalent can be limited to 2000 under 200,250,400 or 800 200g/mol, 1900,1800,1700, 1600, the upper limit of 1500,1400,1300 or 1250g/mol.
It includes in terms of the sum of the hydroxyl of carrier polyol that one or more other embodiments of the present disclosure, which provide carrier polyol, 50% to 100% secondary hydroxyl.Including 50% to 100% all individual values and subrange；Such as with the hydroxyl of carrier polyol Sum meter, carrier polyol may include the upper limit that 100%, 99% or 98% is limited under 50%, 55%, 60% or 96% Secondary hydroxyl.The non-secondary hydroxyl of carrier polyol can be primary hydroxyl.The catalyst that selection is used to form carrier polyol can be to presence Secondary and/or primary hydroxyl percentage in resulting vehicle polyalcohol has influence.For example, in propylene oxide homopolymers In hydroxyl total amount meter, may include and making less than 2% primary hydroxyl with propylene oxide class homopolymer prepared by base metal catalysts There can be at most substantially 8% primary hydroxyl with propylene oxide class homopolymer prepared by double metal cyanide catalyst complex.This public affairs It is triol that one or more embodiments for opening, which provide carrier polyol, be quantity average hydroxyl equivalent is that 900g/mol is arrived 1350g/mol and in terms of the sum of the hydroxyl of carrier polyol, the polyoxypropylene homopolymerization with 95% to 100% secondary hydroxyl Object.
The nominal hydroxy functionality of carrier polyol can be 2.0 to 6.0.Including 2.0 to 6.0 all individual values and sub- model It encloses；Such as the nominal hydroxy functionality of carrier polyol can be to be limited to 6.0,5.5,5.0 under 2.0,2.2,2.5,2.7 or 2.9 Or 4.2 the upper limit.
Carrier polyol can be include the homopolymer of propylene oxide or the polyether polyol of copolymer.For example, carrier Polyalcohol can be the polymer of propylene oxide.The example of copolymer includes but is not limited to that propylene oxide and the random of ethylene oxide are total to Polymers, by polymerizeing the mixture of propylene oxide and ethylene oxide, such as to form polyoxyethelene content with copolymer It is prepared by the polyoxypropylene polyoxyethylene copolymer that total weight is 0.5wt% to 30wt%.Including 0.5wt% to 30wt% All individual values and subrange；Such as with the total weight of copolymer, the polyoxyethylene of polyoxypropylene polyoxyethylene copolymer contains Amount can for be limited under 0.5wt%, 1.0wt%, 2.0wt% or 5.0wt% 30wt%, 28wt%, 25wt%, 20wt% or The upper limit of 15wt%.It includes the propylene oxide containing polymerization and oxidation second that one or more other embodiments of the present disclosure, which provide copolymer, Another end block block copolymerization in one one or more Internal Block and propylene oxide and ethylene oxide in alkene Object.With the total weight of copolymer, holding block can be 0.5wt% to 30wt%.It is all individual including 0.5wt% to 30wt% Value and subrange；Such as with the total weight of copolymer, holding block can be 0.5wt%, 1.0wt%, 2.0wt% or 5.0wt% Under be limited to the upper limit of 30wt%, 28wt%, 25wt%, 20wt% or 15wt%.One or more other embodiments of the present disclosure mention It is triol for carrier polyol, for the total weight of copolymer, the polyoxypropylene and 0.5wt% of 80wt% to 99.5wt% Polyoxyethylene and quantity average hydroxyl equivalent to 20wt% are 900g/mol to 1350g/mol, and with the hydroxyl of copolymer The sum meter of base, the copolymer with 95% to 100% secondary hydroxyl, such as random copolymer or block copolymer.
Carrier polyol can be by making propylene oxide, ethylene oxide and/or oxidation in the presence of one or more initiators Butene polymerization preparation.Initiator may include at least two can alkoxylate hydrogen atom.Hydroxyl, primary amino group, secondary amine and mercapto For containing can alkoxylate hydrogen atom group example.The example of initiator include but is not limited to glycerine, water, ethylene glycol, Propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, cyclohexanedimethanol, methyl amine, ethylamine glycerine, Trimethylolpropane, trimethylolethane, pentaerythrite, erythritol, sucrose, D-sorbite, mannitol, diethanol amine, list Ethanol amine, triethanolamine, ethylenediamine, toluenediamine, propanediamine and a combination thereof.
One kind of multiple additional components can be used to form the dispersion of the PIPA particle in carrier polyol.This kind of additional set Dividing can discuss in such as WO2015/038825 and WO2015/038826.One or more other embodiments of the present disclosure provide one kind A variety of additional components include stabilizer and/or water.
As an example, be formed in the PIPA particle in carrier polyol dispersion can in a batch process, semi-batch process, Continuity method, or combinations thereof execute.Carrier polyol, polyisocyanates, low equivalent hydrogen compound containing isocyanate-reactive can It is added to reaction mixture in any order.For example, for the dispersion for the PIPA particle being formed in carrier polyol, The hydrogen compound containing isocyanate-reactive of low equivalent can occur with reacting for polyisocyanates in the presence of carrier polyol, or The pre-reaction between the pure and mild polyisocyanates of carrier polyol can be performed, and the hydrogenation containing isocyanate-reactive of low equivalent is closed Object can add behind.For example, when forming pre-reaction mixture, method may include by 1 parts by weight to 50 parts by weight Polyisocyanates of the average isocyanate ester equivalent less than 225 and the quantity average hydroxyl equivalent of 100 parts by weight are at least 200g/ The carrier polyol of the secondary hydroxyl of mol and at least 80% combines.Polyisocyanates can with polyether polyol mixing when react with Pre-reaction mixture is generated, unreacted carrier polyol, unreacted polyisocyanates and carrier polyol and more are contained One or more adducts containing isocyanate group of isocyanates.Then, quantity averagely contains isocyanate-reactive hydrogen equivalent The hydrogen compound containing isocyanate-reactive and optionally additional polyisocyanates of low equivalent of the weight less than 80g/mol can be divided It is fitted in pre-reaction mixture, such as makes the hydrogen compound containing isocyanate-reactive that can provide low equivalent to consume pre- anti- Answer the isocyanate group in mixture.For example, the hydrogenation containing isocyanate-reactive that can add 1 to 30 parts of low equivalent is closed Object.The hydrogen compound containing isocyanate-reactive of low equivalent can be reacted with isocyanate group to be formed and be scattered in carrier polyol PIPA particle.Pre-reaction can be by continuously making liquid-carrier polyalcohol and polyisocyanates in mixing head together with the company of being formed The continuous mixture for being introduced into tubular reactor is formed, and the hydrogen compound containing isocyanate-reactive of low equivalent and optionally another Outer polyisocyanates can add in the downstream of tubular reactor.
The dispersion of PIPA particle in carrier polyol forms reaction and can hold under 15 DEG C to 150 DEG C of reaction temperature Row.Including 15 DEG C to 150 DEG C of all individual values and subrange, such as reaction temperature can be to be limited to 150 at 15 DEG C or 20 DEG C DEG C or 130 DEG C of the upper limit.Cooling can be used for maintaining reaction temperature.
Glycol composition disclosed herein includes the total weight with glycol composition, glycol composition The polyester polyol of 1wt% to 98wt%.All individual values of 1wt% to 98wt% including glycol composition and sub- model Enclose, such as with the total weight of glycol composition, polyester polyol can for glycol composition 1wt%, 3wt%, Be limited under 5wt%, 10wt%, 15wt%, 20wt%, 25wt%, 30wt%, 32wt%, 35wt% or 40wt% 98wt%, 95wt%, 90wt%, 85wt%, 80wt%, 75wt%, 70wt%, 68wt%, 65wt%, 60wt%, 55wt%, 50wt% Or the upper limit of 45wt%.One or more other embodiments of the present disclosure provide polyester polyol and are selected from the first polyester polyol, second The combination of polyester polyol and pure and mild second polyester polyol of the first polyester polyols.For example, with the total of glycol composition Poidometer, the first polyester polyol can be 1wt% to the 98wt% of glycol composition；With the total weight of glycol composition Meter, the second polyester polyol can be 1wt% to the 98wt% of glycol composition；Or with the total weight of glycol composition, The combination of pure and mild second polyester polyol of first polyester polyols can be 1wt% to the 98wt% of glycol composition
" polyester " refers to comprising two or more bonded compounds, such as polyalcohol.Polyester described herein is more First alcohol, such as the first polyester polyol and/or the second polyester polyol can contain long-chain fat race base as one or more weights A part of complex structure unit.In one or more embodiments, the structural unit of the base of race containing long-chain fat can be derived from binary Acid or its ester.In one or more embodiments, polyester polyol can contain other structures unit, such as derived from a kind of or more The structural unit of kind glycol, can react with binary acid/ester to form polyester polyol.
Polyester polyol can be formed by a variety of methods.For example, polyester polyol can be such as short by including especially glycol Chain diol, binary acid and/or its ester, triol, it is anti-such as glycerine or trimethyl third and/or tetrol such as tetraacethyl (quadrol) Mixture is answered to be formed.Polyester polyol can be formed by condensation reaction.The example of acid and/or ester includes but is not limited to 1,11- ten One docosandioic acid, 1,12 dodecanedioic acid, 1,13- tridecandioic acid, 1,14- tetracosandioic acid, 1,15- pentacosandioic acid, 1, 16- hexadecandioic acid (hexadecane diacid), 1,17- heptadecane diacid, 1,18- octadecane diacid, 1,19- nonadecandioic acid, 1,20- docosane two Acid, 1,21- eicosane diacid, 1,22- docosandioic acid, 1,23- tricosane diacid, 1,24- tetracosandioic acid or its Any ester, or combinations thereof." short-chain diol " refers to the glycol with 1 to 18 carbon atoms.In one or more embodiments, short Chain diol be C.sub.2-18 alkylene glycols, wherein one or more saturated carbon atoms of alkylene optionally by oxygen, nitrogen, Sulphur or silicon displacement.In some other embodiments, short-chain diol is ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, five It is ethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, four propylene glycol, 1,3- propylene glycol, 1,3 butylene glycol, 1,4- butanediol, new Bis- (2- ethoxy) ethers of pentanediol, 1,5-PD, 1,6- hexylene glycol, 1,4-CHDM, hydroquinone, or to two- (2- hydroxyl-oxethyl) benzene, or combinations thereof.
Polyester polyol may include block, such as such as block copolymer.The example of block includes but is not limited to acrylic acid Polymer, polyurethanes, polyureas, polyanhydride, is substituted polyethylene polymer, polycarbonate or its is any total at polyamide Polymers.
The average functionality of first polyester polyol can be 2.0 to 2.8.Including 2.0 to 2.8 all individual values and sub- model It encloses；Such as first the average functionality of polyester polyol can be the upper limit that 2.8 or 2.7 are limited under 2.0 or 2.1.This average official Energy degree can be calculated as the quotient of the total mole of OH and the total mole of polyalcohol.The hydroxyl value of first polyester polyol can be 215mg KOH/g to 255mg KOH/g.All individual values and subrange for arriving 255mg KOH/g including 215；Such as first is poly- The hydroxyl value of ester polyol can be the upper limit that 255,250 or 245mg KOH/g is limited under 215,220 or 225mg KOH/g.
The average functionality of second polyester polyol can be 2.4 to 3.5.Including 2.4 to 3.5 all individual values and sub- model It encloses；Such as second the average functionality of polyester polyol can be the upper limit that 3.5 or 3.3 are limited under 2.4 or 2.7.Second polyester The hydroxyl value of polyalcohol can be 295mg KOH/g to 335mg KOH/g.Including 295 to 335mg KOH/g it is all it is individual value and Subrange；Such as second polyester polyol hydroxyl value can for be limited under 295,300 or 305mg KOH/g 335,330 or The upper limit of 325mg KOH/g.
Glycol composition disclosed herein may include surfactant.Surfactant includes silicon class compound, such as silicon Ketone oil and organic silicone-copolyether, such as dimethyl silicone polymer and polydimethylsiloxane--polyoxyalkylene block copolymerization Object, for example, polyether-modified dimethyl silicone polymer and a combination thereof.The example of surfactant include silicon dioxide granule and Silica aerogel powder and organic surface active agent such as nonyl phenol ethoxylate.Surfactant is commercially available simultaneously And including with product name such as NIAXTM、DABCOTMAnd TEGOSTABTMEtc. obtained by those.Some embodiments of the present disclosure Surfactant is provided, is 0.1 part to 3.0 parts of total polyalcohol of every 100 parts of glycol compositions when utilized.Including 0.1 part To 3.0 parts of all individual values and subrange；Such as surfactant can be total polyalcohol of every 100 parts of glycol compositions 0.1,3.0,2.5 or 2.0 upper limit is limited under 0.2 or 0.3 part.
Glycol composition disclosed herein may include catalyst.Catalyst can for amine catalyst, metallic catalyst and its Combination.The example of amine catalyst includes pentamethyl diethylene-triamine, triethylamine, tri-butylamine, dimethylethanolamine, N, N, N ', N '-four-methyl ethylenediamine, dimethyl-benzyl amine, N, N, N ', N '-tetramethyl butane diamine, dimethyl cyclohexyl amine, three second two Amine and a combination thereof etc..The example of metallic catalyst includes tin (II) salt of organic carboxyl acid, for example, oxalic acid tin (II), two pungent The dialkyl tin (IV) of sour tin (II), diethyl caproic acid tin (II), stannous octoate and tin dilaurate tin (II) and organic carboxyl acid Salt, for example, dibutyltin diacetate, dibutyl tin dilaurate, dibutyl tin maleate and two acetic acid dioctyl tins, and A combination thereof etc..Surfactant is commercially available and including with product name such as NIAXTM、POLYCATTMAnd DABCOTMEtc. can Those of obtain.One or more other embodiments of the present disclosure provide the combination that catalyst can be at least one amine and metal salt.
Embodiment of the disclosure provides 0.04 part to 8.00 of total polyalcohol that catalyst can be every 100 parts of glycol compositions Part.Including 0.04 part to 8.00 parts of all individual values and subrange；Such as catalyst can be every 100 parts of glycol compositions 8.00,7.50 or 7.00 parts of the upper limit is limited under total 0.04,0.07 or 0.09 part of polyalcohol.
Glycol composition disclosed herein may include fire retardant.A variety of fire retardants known to those skilled in the art. The example of fire retardant is three (2- chloro isopropyl)-phosphates.Fire retardant can be when utilized every 100 parts of glycol compositions Total 4.0 parts to 15.0 parts of polyalcohol.Including 4.0 parts to 15.0 parts of all individual values and subrange；Such as fire retardant can be every 15.0,14.5 or 14.0 parts of the upper limit is limited under 4.0,4.5 or 5.0 parts of total polyalcohol of 100 parts of glycol compositions.
Glycol composition disclosed herein can one or more additional components.It can be used for different application different additional Component and/or different amounts of additional component.The example of additional component include liquid and/or solid pigment, colorant, crosslinking agent, Filler, chain extender, antioxidant, surface modifier, biological retarding agent, release agent and a combination thereof etc..
One or more other embodiments of the present disclosure provide rigid closed-cell foam formulation.Rigid closed-cell foam formulation can wrap Include glycol composition, foaming agent and polyisocyanates disclosed herein.
With the total weight of rigid closed-cell foam formulation, rigid closed-cell foam formulation may include 5wt% to 85wt% Glycol composition.All individual values and subrange including 5wt% to 85wt%；Such as with rigid closed-cell foam formulation Total weight, rigid closed-cell foam formulation may include being limited under 5wt%, 8wt%, 10wt%, 15wt% or 20wt% The glycol composition of the upper limit of 85wt%, 80wt%, 75wt%, 70wt% or 65wt%.
As mentioned, rigid closed-cell foam formulation may include foaming agent.Foaming agent can be physical blowing agent, chemical blowing Agent, or combinations thereof.
Physical blowing agent can help to that rigid closed-cell foam formulation is made to foam.The example of physical blowing agent includes liquid two Carbonoxide；Alkane；Cycloalkane such as pentamethylene, hexamethylene, cyclobutane and its mixture；Other rings at most 7 carbon atoms Alkane；Dialkyl ether, cycloalkylidene ether, fluothane hydrocarbon and its mixture.The example of alkane includes but is not limited to propane, butane, just Butane, iso-butane, pentane, isopentane and a combination thereof.The example of dialkyl ether includes dimethyl ether, methyl ethyl ether, methyl butyl Ether, ether and a combination thereof.The example of cycloalkylidene ether is furans.The example of fluothane hydrocarbon includes but is not limited to fluoroform, difluoro Methane, Difluoroethane, tetrafluoroethane, heptafluoro-propane and a combination thereof.
Some embodiments of the present disclosure provide physical blowing agent, when utilized, can be for every 100 parts in rigid closed-cell foam 0.5 part to 22.0 parts of total polyalcohol in formulation.Including 0.5 part to 22.0 parts of all individual values and subrange；Such as object Haircut infusion can be to be limited under 0.5,1.0 or 2.0 part of every 100 parts total polyalcohols in rigid closed-cell foam formulation 22.0,20.0,17.0,15.0,13.0 or 10.0 parts of the upper limit.
For example, using chemical foaming agent by forming carbon dioxide with reacting for polyisocyanates.Example chemistry Foaming agent is water.Some embodiments of the present disclosure provide chemical foaming agent, are every 100 parts in rigid closed-cell foam when utilized 0.2 part to 5.0 parts of total polyalcohol in formulation.Including 0.2 part to 5.0 parts of all individual values and subrange；Such as chemistry Foaming agent can be limited to 5.0 under 0.2,0.3 or 0.4 part of every 100 parts total polyalcohols in rigid closed-cell foam formulation, 4.8 or 4.6 parts of the upper limit.Some embodiments of the present disclosure provide carbon dioxide can also be via the adduct of carbon dioxide, such as ammonia Carbamate utilizes, and can be added to rigid closed-cell foam formulation.
Rigid closed-cell foam formulation may include polyisocyanates.It can be used for the polyisocyanic acid of rigid closed-cell foam formulation Ester be herein it is previously discussed those, that is, about in carrier polyol PIPA particle dispersion discuss polyisocyanates. The polyisocyanates index of rigid closed-cell foam formulation can be 150 to 500.Including 150 to 500 all individual values and sub- model It encloses；Such as the polyisocyanates index of rigid closed-cell foam formulation can be to be limited to 500,425 or 350 under 150,175 or 200 The upper limit.Polyisocyanates index can be measured as the equivalent of the isocyanates in rigid closed-cell foam formulation divided by hard The total yield of isocyanate-reactive hydrogen in closed-cell foam formulation, multiplied by 100.
Rigid closed-cell foam disclosed herein can be matched by solidification (such as making its reaction) previously discussed rigid closed-cell foam Object preparation processed.As mentioned, rigid closed-cell foam formulation disclosed herein can have the desired multiple solidifications of various applications special Property.
The cream time of rigid closed-cell foam formulation is 3 seconds to 30 seconds.Including 3 to 30 all individual values and sub- model It encloses；Such as the cream time of rigid closed-cell foam formulation can be the upper limit that 30,29 or 28 seconds are limited under 3,4 or 5 seconds.
The gel time of rigid closed-cell foam formulation is 10 seconds to 140 seconds.Including 10 to 140 all individual values and son Range；Such as the gel time of rigid closed-cell foam formulation can be to be limited to 140,120 or 100 seconds under 10,15 or 20 seconds The upper limit.
The tack-free time of rigid closed-cell foam formulation can be 20 seconds to 180 seconds.Including 20 to 180 it is all it is individual value and Subrange；Such as the tack-free time of rigid closed-cell foam formulation can be limited to 180 under 20,25 or 30 seconds, 170,160, 150,140,130,120,110,100,90,80,70,60,55 or 50 seconds upper limits.
Known method preparation can be used in rigid closed-cell foam disclosed herein.These methods may include continuously or discontinuously from By foaming plate hair foam method and molding foaming method, using mixing head or stirring rod presence or absence of air the case where Lower blend components.The output of mixing head can be deposited on conveyer or arrive mold.For plate method, rigid closed-cell foam can It further expands and moves downward rising along conveyer at it, form the continuous hard of the block or foam rubber block that can be cut into desired length Matter closed-cell foam chunk, for further solidification and/or storage and subsequent slice.In discontinuous method, rigid closed-cell foam Formulation can be mixed by head and be poured into container.Using varying pressure in foaming (VPF) side being such as described in US 5,194,453 Method.
One-step method can be utilized by moulding foaming method, and wherein the isocyanates of specific quantity and the remaining rigid closed cell of specific quantity steep It foam formulation formulation group subassembly and mixes, to form mixture.Mixture can be used as offscum and deposit in mold, then Guan Bi mould.Foam is inflatable to fill mold, and the mold then turns on after curing time for demoulding.Curing time It can be between such as 1 minute and 20 minutes.Various solidification temperatures can be used for various applications.
As mentioned, compared with other rigid closed-cell foams, rigid closed-cell foam can have being averaged for improvement (that is, reduction) Cell diameter.The mean cell diameter of rigid closed-cell foam can be 90 microns to 165 microns.Including 90 to 165 microns own Individual values and subrange；Such as the mean cell diameter of rigid closed-cell foam can be to be limited under 90,100,110 or 120 microns 165,160 or 155 microns of the upper limit.
Thermal conductivity of rigid closed-cell foam at a temperature of 10 DEG C of average plates can be every meter of Kelvin of 17 to 24 milliwatt.Including 17 To all individual values and subrange of every meter of Kelvin of 24 milliwatt；Such as heat of rigid closed-cell foam at a temperature of 10 DEG C of average plates Conductance can be the upper limit that 24,23.5 or 23 every meter of Kelvins of milliwatt are limited under 17,19,20.5 or 21 every meter of Kelvins of milliwatt.
Thermal conductivity of rigid closed-cell foam at a temperature of 24 DEG C of average plates can be every meter of Kelvin of 18 to 25 milliwatt.Including 18 To all individual values and subrange of every meter of Kelvin of 25 milliwatt；Such as heat of rigid closed-cell foam at a temperature of 24 DEG C of average plates Conductance can be the upper limit that 25,25.5 or 24 every meter of Kelvins of milliwatt are limited under 18,19,21.5 or 22 every meter of Kelvins of milliwatt.
The open volume percentage of rigid closed-cell foam can be 1 volume % to 15 volume %.Including 1 volume % to 15 bodies All individual values and subrange of product %；Such as the open volume percentage of rigid closed-cell foam can for 1 volume %, 2 volume %, 15 volume %, 14 volume % or 13 volume % are limited under 3 volume %, 4 volume %, 5 volume %, 6 volume % or 7 volume % The upper limit.
The free foaming density of rigid closed-cell foam can be 21kg/m3To 50kg/m3.Including 21kg/m3To 50kg/m3's All individual values and subrange；Such as the free foaming density of rigid closed-cell foam can be 21kg/m3、23kg/m3、25kg/m3、 27kg/m3Or 30kg/m3On be limited to 50kg/m3、45kg/m3Or 40kg/m3Lower limit.
Example
In instances, using the term of a variety of materials and title, including for example following:
(polyester polyol is formed polyalcohol A by phthalic anhydride, diethylene glycol and long chain fatty acids；Average functionality 2.0；Hydroxyl value 235mg KOH/g)；Polyalcohol B (polyester polyol, by terephthalic acid (TPA), diethylene glycol, polyethylene glycol and third Triol is formed；Average functionality 2.4；Hydroxyl value 315mg KOH/g)；Polyalcohol C (the polyisocyanates in carrier polyol The dispersion of addition polymerization particle, solid content are substantially 20%.The average grain diameter of the polyisocyanate polyaddition particle of 90 weight % Less than 5 microns, measured with Beckman Coulter Inc.'s (Beckman Coulter) LS particle size analyzer.The mark of carrier polyol Hydroxy functionality is referred to as 3.The hydroxyl value of carrier polyol is 56KOH/g.Carrier polyol is 3000 molecular weight, nominal trifunctional Poly- (propylene oxide) has at least 90% secondary hydroxyl.Polyisocyanate polyaddition particle is triethanolamine and toluene di-isocyanate(TDI) 2,4- and 2,6- isomers 80/20 mixture reaction product.Polyalcohol C is such as in WO2015/038825 and WO2015/ 038826) it is prepared described in；Polyalcohol D (polyether polyol；Polyalcohol/polypropylene oxide that glycerine causes, hydroxyl value 55mg KOH/g, nominal hydroxy function 3.0)；NIAXTML-6633 (polyether-modified polysiloxanes；Surfactant；It is purchased from MOMENTIVETM)；DABCOTM(the potassium acetate in diethylene glycol of K 2097；Catalyst；It is purchased from air products (Air Products))；POLYCATTM5 (PMDETA-N, N, N ', N ", N "-five methyl diethylentriamines；Catalyst；It is purchased from sky Gas product)；VORACORTMCM822 (the 2 ethyl hexanoic acid potassium in diethylene glycol and triethyl phosphate)；It is purchased from Tao Shiization Company (The Dow ChemicalCompany))；Three (2- chloro isopropyl)-phosphate (fire retardants；It is purchased from ICL)； VORANATETMM 600 (polymeric methylene diphenyl diisocyanate, NCO 30.5%；It is purchased from Dow Chemical).
It is following to form example 1, glycol composition.By polyalcohol A (64.77 parts), polyalcohol B (21.37 parts) and polynary Alcohol C (dispersion (10.00 parts) of the polyisocyanate polyaddition particle in carrier polyol) is combined to provide reality in a reservoir Example 1.By NIAXTML-6633 (1.97 parts), DABCOTMK 2097 (0.44 part), POLYCATTM5 (0.27 parts), VORACORTM CM822 (2.81 parts), three (2- chloro isopropyl)-phosphates (10.72 parts) and water (0.44 part) are added to example 1.With example 1 Total weight, example 1 include the polyalcohol B of the polyalcohol A and 21.37wt% of 64.77wt%.
It is following to form example 2, rigid foam formulation.By example 1 and VORANATETM(167.5 parts) of M 600 combinations.It is real The composition of example 2 is reported in table 1.For example 2, VORANATE will be removedTMAll components except M600 are in high-pressure injection machine It is combined in first feed containers of (Cannon AP-40), and by VORANATETMM 600 is placed on the of high-pressure injection machine In two feed containers.Temperature and 15 of the high-pressure injection machine at 20 DEG C ± 2 DEG C operates under the pressure of 000kPa ± 2000kPa, simultaneously Polyisocyanates index maintain 250 under to generate example 3, rigid foam.
If example 2 forms comparative example A, wherein change into using polyalcohol D rather than polyalcohol C.The group of comparative example A Object is closed to report in table 1.If example 3 forms comparative example B, rigid foam, wherein change into using comparative example A rather than reality Example 2.
Table 1
As mentioned, example 3, rigid closed-cell foam are formed by example 2, and comparative example B, rigid closed-cell foam, by Comparative example A is formed；In addition, as comparative example B forms comparative example C, wherein changing into does not include polyalcohol D.Pass through scanning The mean cell diameter of electron-microscopic analysis measurement example 3 and comparative example B-C: by the part of example 3 and comparative example B-C It is respectively installed to retainer, it is dry, and sputtered 250 seconds at 20 μ A with gold with Quorum Q150R-S gold sputtering coating machine. Philips XL30FEGSEM scanning electron microscope and the secondary electron for imaging detect under the acceleration voltage of 20kV Device analyzes coated part.As a result it is reported in table 2.
Table 2
The data of table 2 illustrate that compared with comparative example B-C, example 3 has the mean cell diameter for improving (that is, smaller).
According to ISO 12939/DIN 52612, with LaserComp Fox 200 at a temperature of 10 DEG C and 24 DEG C of average plate Measure the thermal conductivity of example 3 and comparative example B.As a result it is reported in table 3.
Table 3
The data explanation of table 3 is compared with comparative example B, both mean temperature and 24 DEG C of mean temperature for 10 DEG C, Example 3 has improved thermal conductivity.
In addition, example 3 and the corresponding portion of comparative example B are cured as free foaming case foam, wherein according to ASTM D 6226 measurement open volume percentages.Pass through following Observe and measure cream time, gel time and tack-free time.Cream time: Due to bubble nucleating, liquid reaction mixture color becomes the limpider time.Gel time: foam has developed dimensionally stable Sufficient intensity, and spatula is when the time for being inserted into and pulling since when foam quickly removes cord.Tack-free time: when light Foam surface (epidermis) loses the time of its viscosity when lightly touching.Free foaming density is at wooden case (30 × 20 × 25cm of size) It is measured on the 25cm high foam sample of middle preparation.Cutting sample to be after foaming 20 minutes to obtain core foam sample, and with kg/m3Measure its density.As a result it reports in table 4.
Table 4
Example 3 Comparative example B
Open volume % 11 volume % 12 volume %
Cream time 11 seconds 11 seconds
Gel time 25 seconds 25 seconds
Tack-free time 34 seconds 33 seconds
Free foaming density 33.5kg/m3 33.5kg/m3
Both the data illustrated example 3 of table 3 and comparative example B are closed-cell foam.In addition, compared with comparative example B, it is real Example 3 has the open volume % for improving (that is, reduction).This data instruction PIPA particle does not destroy abscess, such as in SAN.
In addition, when the data illustrated example 3 and comparative example B of table 4 have comparable cream time, gel time and disappear viscous Between.This instruction is when using glycol composition, (it includes the polyisocyanates in carrier polyol as disclosed herein The dispersion of addition polymerization particle) when these curing characteristics it is adversely not impacted.

Claims (15)

1. a kind of glycol composition, it includes:
The dispersion of polyisocyanate polyaddition particle in carrier polyol, wherein the polyisocyanate polyaddition particle is flat Equal partial size is 0.1 to 10.0 microns, and with the total weight of the dispersion, the solid content of the dispersion is 5wt% To 50wt%；With
With the total weight of the glycol composition, the polyester polyol of 1wt% to the 98wt% of the glycol composition.
2. glycol composition according to claim 1, wherein the polyester polyol is selected from the first polyester polyol, the The combination of dimerization ester polyol and pure and mild second polyester polyol of first polyester polyols.
3. glycol composition according to claim 2, wherein the average functionality of first polyester polyol is 2.0 To 2.8, and hydroxyl value is 215mg KOH/g to 255mg KOH/g.
4. the glycol composition according to any one of claim 2 to 3, wherein second polyester polyol is averaged Degree of functionality is 2.4 to 3.5, and hydroxyl value is 295mg KOH/g to 335mg KOH/g.
5. the glycol composition according to any one of claim 2 to 4, wherein the nominal hydroxy of the carrier polyol Degree of functionality is 2.0 to 6.0.
6. the glycol composition according to any one of claim 2 to 5, wherein the hydroxyl value of the carrier polyol is 25mg KOH/g to 350mg KOH/g.
7. according to claim 1 to glycol composition described in any one of 6, wherein the carrier polyol is with oxidation third The polyalcohol that the glycerine that alkene is formed causes.
8. according to claim 1 to glycol composition described in any one of 7, wherein the glycol composition further wraps Containing surfactant.
9. according to claim 1 to glycol composition described in any one of 8, wherein the glycol composition further wraps Containing catalyst.
10. according to claim 1 to glycol composition described in any one of 9, wherein the glycol composition is further Include fire retardant.
11. a kind of rigid closed-cell foam formulation, it includes:
According to claim 1 to glycol composition described in any one of 10；
Foaming agent；With
Polyisocyanates.
12. rigid closed-cell foam formulation according to claim 11, wherein the polyisocyanate cyanogen of the rigid foam formulation Acid esters index is 150 to 500.
13. a kind of rigid closed cell that rigid foam formulation is formed as described according to claim 1 any one of 1 to 12 bubble Foam, wherein the mean cell diameter of the rigid closed-cell foam is 90 microns to 165 microns.
14. rigid closed-cell foam according to claim 13, wherein the free foaming density of the rigid closed-cell foam is 21kg/m3To 50kg/m3。
15. a kind of method for being used to form rigid closed-cell foam, it includes:
Solidify any one of rigid closed-cell foam formulation described in 1 to 12 according to claim 1.
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